I currently live in Norfolk, potentially moving to Ecuador within the coming year.

So I am entertaining the idea of purchasing a boat locally, sailing/motoring south via ICW, island hopping the Caribbean, then to Panama, finally south to Bahia. Knowing this will be no easy feat, I am asking for your thoughts (good or bad) or any valuable experiences to learn from.
Estimated time? Is this realistic or just another crazy idea!?

Not crazy but allow a year to get to Ecuador. Both the Caribbean and the Pacific coast line south are "seasonally dependent." Only during a short period each year are the conditions reasonable to be heading that way. So you will have plenty of time to kill in the various islands/countries along the way.

Three of the boats that I sailed with off and on down from Mazatlin to Panama, departed Panama and took a wide loop out into the Pacific to approach Ecuador from the south as the main current travels counter-clockwise in the Southren Hemisphere.
I believe they also required a local guide to travel thru the surf lines.

. . . You would be best off getting a boat in California and sailing south after a few months....

Now, that's the best suggestion yet. You avoid a lot of lost time waiting for the best "season" in two different basins and chop your transit time significantly. Not mention see an area not normally traveled by "easterners."